Seller's Agent in 2026
Kasey Hilyard
PALM CIRCLE REALTY
(407) 488-9879
130 Total Sales
2756 Sheriff Way Winter Park, FL 32792
Winter Park Area
3
Beds
2
Baths
1,812
Sq Ft
8,758
Sq Ft Lot
Highlights
- Wine Refrigerator
- Community Pool
- Living Room
- Winter Park High Rated A
- 2 Car Attached Garage
- Laundry Room
About This Home
As of July 2026**$30,000 Price Improvement!! Welcome to your beautifully updated slice of the Florida Dream here in Winter Park! Perfectly positioned on a desirable corner lot, this thoughtfully renovated home blends modern design, comfort, and functionality - minutes away from Advent Health, Park Avenue, and Schools! From the moment you step inside, you’ll notice the extensive tile flooring, upgraded lighting, and stylish finishes throughout. The heart of the home is the stunning RENOVATED KITCHEN featuring QUARTZ countertops, rich NAVY cabinetry, stainless steel appliances, and a gorgeous wine & coffee bar complete with a built-in WINE FRIDGE—perfect for entertaining or slow Florida mornings at home. Need space to work or unwind? The dedicated OFFICE with MODERN BARN DOORS creates the ideal work-from-home setup, while the additional BONUS ROOM offers endless flexibility as a playroom, reading retreat, media space, or hobby room. Down the hall, the spacious and serene Primary Suite invites you to unwind in the renovated, spa-inspired rain showerhead for a relaxing start or finish to your day. The 2nd bedroom has been dubbed the "Hotel Room" by guests because of its larger size and additional sitting area. This space is perfect for MULTIGENERATIONAL LIVING, whether they are coming home for the summer, guests visiting Central Florida on vacation, or extended family needing a space of their own! The 3rd bedroom is across the hall from the Primary and features laminate flooring, so you truly have 3 dedicated bedrooms PLUS an office! Practical upgrades set this home apart from others in the community, including CUSTOM BLINDS Throughout & 5 1/4 INCH BASEBOARDS in the main living areas, an indoor, heated & cooled LAUNDRY ROOM, Replaced A/C (Inside 2020, Outside 2019), NEW ROOF (2022), PVC REPIPE (2018), NEW SEWER, NEWLY FENCED BACKYARD (2022), WIFI Garage Opener (2020)a storage shed, and a NEW (2021) COVERED & SCREENED LANAI with waterproof and weatherproof interlocking flooring, designed for year-round indoor/outdoor living enjoyment. This move-in-ready abode delivers the perfect balance of style and everyday living! Whether you’re hosting friends, working remotely, or simply enjoying the Florida lifestyle, this remarkable gem is located blocks away from Cady Way Trail and Ward Park, and just minutes from the award-winning restaurants on Park Avenue, and in the Baldwin Park & Mills50 shopping districts! Don't sleep on this one, call and schedule your private showing today!
Last Agent to Sell the Property
PALM CIRCLE REALTY Brokerage Phone: 352-988-4975 License #3329311 Listed on: 05/12/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,547
Year Built
- Built in 1965
Lot Details
- 8,758 Sq Ft Lot
- North Facing Home
- Property is zoned R-1A
Parking
- 2 Car Attached Garage
Home Design
- Slab Foundation
- Shingle Roof
- Block Exterior
Interior Spaces
- 1,812 Sq Ft Home
- Ceiling Fan
- Living Room
- Dining Room
- Tile Flooring
Kitchen
- Range
- Microwave
- Dishwasher
- Wine Refrigerator
Bedrooms and Bathrooms
- 3 Bedrooms
- 2 Full Bathrooms
Laundry
- Laundry Room
- Dryer
- Washer
Schools
- Aloma Elementary School
- Glenridge Middle School
- Winter Park High School
Utilities
- Central Heating and Cooling System
- Cable TV Available
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 1 / C
- Assessor Parcel Number 09-22-30-9427-03-010
Community Details
Overview
- Property has a Home Owners Association
- Peter Mason Association, Phone Number (407) 671-0785
- Visit Association Website
- Winter Park Pines Subdivision
Recreation
- Community Pool
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Mar 13, 2018
Closed on
Apr 30, 2018
Sold by
Bought by
Seller's Agent
Jake Johnson
SHORES REAL ESTATE
Buyer's Agent
Darrell Nunnelley
VINTAGE REALTY GROUP LLC
List Price
$362,329
Sold Price
$355,000
Premium/Discount to List
-$7,329
-2.02%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
6.96%
Original Mortgage
$319,500
Interest Rate
4.4%
Mortgage Type
New Conventional
Purchase Details
Closed on
Feb 26, 2016
Sold by
Bought by
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$275,500
Interest Rate
3.81%
Mortgage Type
New Conventional
Purchase Details
Closed on
Dec 28, 1998
Sold by
Bought by
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Home Values in the Area
Average Home Value in this Area
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $355,000 | Attorney | |
| Warranty Deed | $290,000 | Leading Edge Title Partne | |
| Warranty Deed | $108,000 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $290,000 | New Conventional | |
| Closed | $319,500 | New Conventional | |
| Previous Owner | $275,500 | New Conventional | |
| Previous Owner | $154,500 | Credit Line Revolving |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 07/08/2026 07/08/26 | Sold | $588,000 | -1.2% | $325 / Sq Ft | |
| 06/06/2026 06/06/26 | Pending | -- | -- | -- | |
| 06/05/2026 06/05/26 | Price Changed | $595,000 | -4.8% | $328 / Sq Ft | |
| 05/12/2026 05/12/26 | For Sale | $625,000 | +76.1% | $345 / Sq Ft | |
| 04/30/2018 04/30/18 | Sold | $355,000 | -2.0% | $196 / Sq Ft | View Prior Sale |
| 03/17/2018 03/17/18 | Pending | -- | -- | -- | |
| 03/13/2018 03/13/18 | For Sale | $362,329 | -- | $200 / Sq Ft |
Source: Stellar MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $5,547 | $366,591 | ||
| 2025 | $5,547 | $366,591 | ||
| 2024 | $4,932 | $356,953 | ||
| 2023 | $4,932 | $336,789 | $0 | $0 |
| 2022 | $4,729 | $325,038 | $0 | $0 |
| 2021 | $4,651 | $315,571 | $0 | $0 |
| 2020 | $4,430 | $311,214 | $0 | $0 |
| 2019 | $4,562 | $304,217 | $165,000 | $139,217 |
| 2018 | $3,760 | $251,913 | $0 | $0 |
| 2017 | $3,702 | $246,732 | $145,000 | $101,732 |
| 2016 | $3,959 | $243,945 | $130,000 | $113,945 |
| 2015 | $3,553 | $202,319 | $90,000 | $112,319 |
| 2014 | $3,252 | $174,427 | $75,000 | $99,427 |
Source: Public Records
Agents Affiliated with this Home
-
Kasey Hilyard
-
Jeff Taulbee
Buyer's Agent in 2026
Jeff Taulbee
CHARLES RUTENBERG REALTY ORLANDO
(407) 619-0101
103 Total Sales
-
Jake Johnson
Seller's Agent in 2018
Jake Johnson
SHORES REAL ESTATE
(407) 973-2040
32 Total Sales
-
Darrell Nunnelley
Buyer's Agent in 2018
Darrell Nunnelley
VINTAGE REALTY GROUP LLC
(407) 467-8069
100 Total Sales
Map
Source: Stellar MLS
MLS Number: O6402570
APN: 09-2230-9427-03-010
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All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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